Reese Harper, CFP®
Reese Harper, CFP®

Article's Author

If You Jump Off the Cliff by Reese Harper

The Snake River in Idaho has some great cliff jumping spots. I still remember the dread, inching my feet closer to the edge, peering into the dark water, and wondering if this jump was too dangerous. Would I smash my knees into my face when I hit the water? Was there a rock beneath the surface?

The perfect jump isn’t the highest jump, or the craziest jump. In fact, one of the most epic jumps I can remember was watching my daughter, who mustered up the courage to jump about eight feet off a rock in Hawaii. What made it beautiful to me was that it was just slightly outside of her comfort zone, and she jumped, despite the uncertainty.

Although I’m no expert cliff jumper, I learned a few things that helped me avoid serious injury when jumping:

Never go cliff jumping alone.

Make sure the water is deep enough.

You may experience some intense water pressure; this is normal.

Wear sneakers or water shoes.

Keep your body tight and streamline when you jump.

Blow out through your nose.

Preparation creates confidence, which is key.

These lessons helped protect me, and increased my odds of living a healthy, long life. But despite all these protective lessons, you can’t de-risk it all. My career and parenting have been more like that for me.

When I decided to leave music, the only home I had ever known, and navigate the “treacherous waters” of personal finance, I was really scared. When I took on venture capital for the first time, or decided to leave my job at Northwestern Mutual and boot-strap my first startup, I was scared. When I decided to join a new faith community that was different from my heritage, again, I was scared.

And despite all the research, preparation, and risk management, which was SO important, I hit a point where I only had one option left:


Today, I’m writing a quick post to those who might be standing on the edge. I’ve received generous advice from other entrepreneurs over the years, and when I write, I really like to try to pay it forward. This helps others minimize risk, and optimize for a healthy, enjoyable life, whatever their personal values and purpose are inspiring them to do.

Lesson #1: Support your mental and physical health with coaches, therapists, personal trainers, and even a nutritionist. And a dog.

At some point, all of these folks (and Teddy)

have helped me avoid injury and keep pushing myself to higher heights.

Fellow entrepreneurs told me about all of the aches, physical and mental, that I would experience. They warned me that no matter how prepared I thought I was, it was going to be the hardest thing I had ever done. For me, I concluded that I would rather be under pressure than to have never tried to build what I could see in my head. So these “team members” helped make the vision possible.

Through their continued support, I am better able to harness my excitement and energy for building something new, and improving the world around me. There are some really dark days, and I don’t think I would have made it as far without these supportive friends. I think my physical, relational, and mental injuries would have been far more severe.

Lesson #2: Learn to enjoy living with uncertainty.

I used to be really risk-averse, and I worried a lot when I couldn’t see the finish line. But over time, I’ve learned to sit with the difficulty, and learned to love the challenge of that struggle. The uncertainty, it turns out, has been a real gift.

I enjoy standing on the edge of the cliff, not knowing how everything will turn out.

As prepared as I try to be, the future is always uncertain. Hold on to your vision, your beliefs, and your commitment to a better world.

Lesson #3: Take time for fun.

Taking the time to travel, even if it’s just a short trip to a place that gives you energy, can be transformative. Sometimes I just hop in the car and drive to my favorite gelato shop on 9th and 9th to pick up a lemon gelato, coconut sticky rice gelato, or whiskey bourbon gelato, on a Tuesday.

When the budget was tight, I remember driving to Moab for a few days with my boys and my mountain bike. We took a hummer ride through some of the early petroglyphs and fossils in the area. Those memories have a sort of reverence for me.

I really appreciate that I tried to have fun along the way, mostly with the simple things, stuff I could afford comfortably. Sometimes it was just a simple game of Jenga with my daughter, and other times it was an epic backcountry ski trip for a few hours in the morning with Carl. Now, life is a beautiful tapestry of memories, and I can look back on them during really hard times and realize that it wasn’t all hard.

Lesson #4: Focus on building a team.

It’s such a gift to witness people help shoulder the load. I’ve never worked with so many smart colleagues – they are all my superiors in their own unique areas of specialization.

I look back, and see how building a great team wasn’t something I could just do by willing it into existence. I didn’t have the resume, pedigree, or network early on to recruit the most skilled folks in every area. But what I did have was the discipline to surround myself with people who gave me energy. People who were not toxic, for me, and folks who just showed up and gave it everything they had.

As time has passed, and the venture was de-risked, more highly skilled folks became affordable. But early on, it just wasn’t that way.

For me, no financial investment was more valuable, and no emotional investment was more rewarding, than sharing the journey with people I love.

Lesson # 5: Write, communicate, and share your learnings with your people. Especially if you don’t think you’re a writer.

In the world of social media, it’s easy to think that the only writing that matters is the writing that everyone is going to see.

But some of my most meaningful, even sacred writing, has been in private letters to my kids, or texts to a friend, or even internal memos to teammates. Your immediate circle is so special, and your thoughts, just for them, could be the most impactful.

My best ideas have come after long periods of difficult writing. If you can write things out, in really simple, clear language, you can change one person’s life. And you can change the world.

I used to podcast more than I write, so I practiced talking a lot. Both mediums have their benefits—but writing, for me, has been the most clear lever I can pull. When done well, it’s a very precise and sharp instrument that clarifies confusing ideas.

Although writing is really hard to produce, it’s probably my preferred personal medium for telling someone that I appreciate them. It’s so precise, and concrete, that you can really communicate with power. The drafting process is hard, but it will teach you about who you are. The editing process is painful, but it will show you what you really care about. And help you transform and evolve. Ignore the fear of criticism, and forget about being misunderstood. Jump off that cliff and hit the publish button. You’re not writing only for yourself, your brand, or your income—you’re writing because your experiences and stories will help at least one other person out there.

Writing is a gift—your words might not change the world, but they will change someone’s life. Share your truth.

To wrap, I want to say thanks to each of you for all of your support recently. It’s been hard to maintain a consistent writing practice, and start conversations that are authentic to my experience, and also helpful to you. I’ve been inspired by all the things you are creating.

Taking an idea and bringing it to life is a beautiful part of human existence. It’s scary to look over the edge of the cliff. But humans do such amazing things. Their creations in music, literature, technology, services, non-profit work, and raising healthy human beings are incredible. Almost every endeavor, especially the ones that bring about the most global change, involve jumping off a cliff, when you’d rather climb back down to safety. I’m always glad when I take the jump—no regrets.

I hope this inspires you to find the right “next jump” in your life too.

You got this.

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